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| Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic alcohol, with the chemical formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colorless and flammable liquid with a distinctive alcoholic odor similar to that of ethanol (potable alcohol), but is more acutely toxic than the latter.
Methanol acquired the name wood alcohol because it was once produced through destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.
Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialized chemicals. |
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Read full article at Wikipedia
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| InChI=1S/CH4O/c1-2/h2H,1H3 |
| OKKJLVBELUTLKV-UHFFFAOYSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Mycoplasma genitalium
(NCBI:txid2097)
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See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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Homo sapiens
(NCBI:txid9606)
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Found in
saliva
(UBERON:0001836).
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
urine
(BTO:0001419).
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
blood
(UBERON:0000178).
See:
Baselt, RC. Disposition of toxic drugs and chemicals in man. 1982. 2nd edition. Biomedical Publications. Davis, CA.
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Homo sapiens
(NCBI:txid9606)
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Found in
breast milk
(ENVO:02000031).
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
cerebrospinal fluid
(UBERON:0001359).
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
faeces
(UBERON:0001988).
See:
PubMed
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amphiprotic solvent
Self-ionizing solvent possessing both characteristics of Bronsted acids and bases.
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Mycoplasma genitalium metabolite
Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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amphiprotic solvent
Self-ionizing solvent possessing both characteristics of Bronsted acids and bases.
fuel
An energy-rich substance that can be transformed with release of usable energy.
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View more via ChEBI Ontology
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carbinol
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ChemIDplus
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CH3OH
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ChEBI
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MeOH
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ChEBI
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Methanol
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KEGG COMPOUND
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METHANOL
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PDBeChem
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methanol
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UniProt
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Methyl alcohol
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KEGG COMPOUND
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Methylalkohol
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NIST Chemistry WebBook
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spirit of wood
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HMDB
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wood alcohol
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ChemIDplus
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wood naphtha
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ChemIDplus
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wood spirit
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NIST Chemistry WebBook
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C00132
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KEGG COMPOUND
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c0132
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UM-BBD
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D02309
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KEGG DRUG
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HMDB0001875
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HMDB
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Methanol
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Wikipedia
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METOH
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MetaCyc
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MOH
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PDBeChem
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| View more database links |
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1098229
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Reaxys Registry Number
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Reaxys
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449
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Gmelin Registry Number
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Gmelin
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67-56-1
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CAS Registry Number
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NIST Chemistry WebBook
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67-56-1
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CAS Registry Number
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ChemIDplus
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Morinaga O, Uto T, Yuan CS, Tanaka H, Shoyama Y (2010)
Evaluation of a new eastern blotting technique for the analysis of ginsenoside Re in American ginseng berry pulp extracts.
Fitoterapia 81, 284-288 [PubMed:19850112]
[show Abstract]
A new eastern blotting technique has been established for ginsenoside Re (G-Re) contained in American ginseng berry pulp extracts. G-Re in American ginseng berry pulp was extracted using 100% methanol, 100% ethanol, 50% aqueous methanol, and 50% aqueous ethanol. The combined crude extracts were applied onto a polyethersulfone membrane and developed using the methanol-water-acetic acid solvent system (45:55:1 v/v). Separated components were immunostained using anti-G-Re monoclonal antibody. G-Re was first specifically detected and then quantitatively analyzed using NIH Imaging software. We also confirmed that the most suitable solvent was 50% aqueous methanol for extracting G-Re from American ginseng berry pulp. | Macías-Sánchez MD, Mantell C, Rodríguez M, Martínez de la Ossa E, Lubián LM, Montero O (2009)
Comparison of supercritical fluid and ultrasound-assisted extraction of carotenoids and chlorophyll a from Dunaliella salina.
Talanta 77, 948-952 [PubMed:19064074]
[show Abstract]
In the work described here the extraction processes of carotenoids and chlorophylls were analysed using two extraction techniques, namely ultrasound-assisted extraction and supercritical fluid extraction, and the results are compared. The solvents used for the ultrasound-assisted extraction were N,N'-dimethylformamide and methanol and for the supercritical fluid extraction, carbon dioxide. The raw material studied was Dunaliella salina, a microalgae characterized by the high levels of carotenoids present in its cellular structure. The results indicate that the supercritical fluid extraction process is comparable to the ultrasound-assisted extraction when methanol is used as solvent. In addition, the supercritical extraction process is more selective for the recovery of carotenoids than the conventional technique since it leads to higher values for the ratio carotenoids/chlorophylls. Finally, the effects of pressure and temperature on the extraction yields of the supercritical fluid extraction process were studied. | Sasirekha V, Umadevi M, Ramakrishnan V (2008)
Solvatochromic study of 1,2-dihydroxyanthraquinone in neat and binary solvent mixtures.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 69, 148-155 [PubMed:17451998]
[show Abstract]
Preferential solvation of a solvatochromic probe has been studied in binary mixtures comprising of a non-protic and a protic solvent. The non-protic solvents employed are carbon tetrachloride (CCl(4)), acetonitrile (AcN) and N,N-dimethyl formamide (DMF) and the protic solvents are methanol (MeOH) and ethanol (EtOH). The probe molecule exhibits different spectroscopic characteristics depending upon the properties of the solubilizing media. The observed spectral features provide an indication of the microenvironment immediately surrounding the probe. Solvatochromic shifts of the ground and excited states of the probe were analysed by monitoring the charge transfer absorption band and the fluorescence emission spectra in terms of the solute-solvent and solvent-solvent interactions. Fluorescence emission spectra show the dual emission due to excited state proton transfer nature of the probe molecule. The effect of solvent and the excitation energy on dual emission are also studied. The observed magnitude of the Stokes shift in the above solvents has been used to deduce experimentally the dipole moment ratio of the probe molecule for the excited state to the ground state. The dipole moment of excited state is higher than the ground state. | Turner C, Spanel P, Smith D (2006)
A longitudinal study of methanol in the exhaled breath of 30 healthy volunteers using selected ion flow tube mass spectrometry, SIFT-MS.
Physiological measurement 27, 637-648 [PubMed:16705261]
[show Abstract]
Selected ion flow tube mass spectrometry, SIFT-MS, has been used to monitor the volatile compounds in the exhaled breath of 30 volunteers (19 male, 11 female) over a six-month period. Volunteers provided breath samples each week between 8:45 am and 1 pm (before lunch), and the concentrations of several trace compounds were obtained. In this paper the focus is on methanol in breath. The median methanol level determined using the H(3)O(+) precursor ions for all samples was 461 parts-per-billion (ppb), the concentrations for all the samples ranging from 32 to 1684 ppb. The distribution of breath methanol concentration is seen to be log-normal for this healthy population; the geometric mean was 450 ppb, close to the median value, and the multiplicative (geometric) standard deviation was 1.62. Breath methanol is not correlated with age, breath ethanol or ethanol consumed in the previous 24 h, but there was an inverse correlation with body mass index (BMI) for the cohort of volunteers recruited for this study. Observed breath methanol levels are well compatible with the previously published blood methanol levels. Some tentative suggestions are made concerning the origin of endogenous methanol. | Vosmanská M, Sýkora D, Fähnrich J, Kovárová M, Volka K (2005)
Extraction of p-hydroxyacetophenone and catechin from Norway spruce needles. Comparison of different extraction solvents.
Analytical and bioanalytical chemistry 382, 1135-1140 [PubMed:15906011]
[show Abstract]
The phenolic compounds p-hydroxyacetophenone and catechin have been extracted from Norway spruce needles with pure methanol, 80 and 50% (v/v) aqueous methanol, pure acetonitrile, 80% (v/v) aqueous acetonitrile, and pure water. Extraction efficiency of the individual solvents was compared. Although 80% aqueous methanol is the solvent most frequently used for extraction of soluble phenolic compounds from needles, it was found that pure methanol is a more suitable extraction solvent. Surprisingly, a two-step procedure based on the extraction of crushed needles with water then re-extraction with methanol proved a good alternative to direct extraction with methanol. Extraction of uncrushed spruce needles might indicate that relatively more p-hydroxyacetophenone than catechin was located in the surface layer of the needle. | Macià A, Borrull F, Aguilar C, Calull M (2004)
Application of capillary electrophoresis with different sample stacking strategies for the determination of a group of nonsteroidal anti-inflammatory drugs in the low microg x L(-1) concentration range.
Electrophoresis 25, 428-436 [PubMed:14760634]
[show Abstract]
Several on-column sample preconcentration modes--large-volume sample stacking using the EOF pump (LVSEP), LVSEP with anion-selective exhaustive injection (LVSEP-ASEI) and field-amplified sample injection with sample matrix removal using the electroosmotic flow (EOF) pump (FAEP)--were used to analyze some nonsteroidal anti-inflammatory drugs (NSAIDs) by capillary electrophoresis, and then compared. Methanol was the background electrolyte solvent to suppress the EOF. The effect of the type and length of the solvent plug, and the sample injection time were investigated in FAEP to determine the conditions that provided the best response. LVSEP, LVSEP-ASEI, and FAEP improved the sensitivity of the peak area by 100-, 1200-, and 1800-fold, respectively. The methodology developed, in combination with solid-phase extraction (SPE), was applied to the analysis of water samples. | Smith AK, Goff HD, Sun BD (2004)
Freeze-substitution and low-temperature embedding of dairy products for transmission electron microscopy.
Journal of microscopy 213, 63-69 [PubMed:14678513]
[show Abstract]
Dairy products are comprised largely of fat, air and water, which makes it difficult to preserve their ultrastructure for electron microscopy. Keeping the samples frozen throughout fixation and embedding protects the structure and distribution of the components of emulsions and foams. Therefore, dairy products were freeze-substituted and embedded at low temperature (-20 degrees C) to prepare them for transmission electron microscopy. Whipped cream, ice cream mix and dairy/non-dairy mixed systems were frozen by plunging in propane, at its boiling point (-187 degrees C). Ice cream, because it is already frozen, was fractured into 1-mm3 pieces in liquid nitrogen and then added to frozen fixative (-196 degrees C). Fixative solution consisted of glutaraldehyde, osmium tetroxide and uranyl acetate dissolved in either methanol or acetone. When material was to be stained after sectioning the fixative was limited to glutaraldehyde in methanol. The temperature was increased step-wise from -80 to -20 degrees C. Solvent was replaced with resin; the polar resin Lowicryl HM4, the non-polar resin Lowicryl HM20, LR White and LR Gold were tested. Samples were embedded and polymerized at -20 degrees C using ultraviolet light to cross-link the resin. Methanol proved to be the most effective solvent for substituting the ice; the hydrophobic resin Lowicryl HM20 was the most effective resin for retaining fat structure following osmium fixation. | Chong CF (2004)
Methanol is a highly toxic alcohol.
Resuscitation 61, 368-369 [PubMed:15172721] | Sannino F, Gianfreda L (2001)
Pesticide influence on soil enzymatic activities.
Chemosphere 45, 417-425 [PubMed:11680737]
[show Abstract]
The influence of four pesticides, e.g. glyphosate, paraquat, atrazine, and carbaryl, on the activities of invertase, urease and phosphatase of twenty-two soils, numbered as 1-22, was investigated. Soils displayed a general variability of enzyme activities with invertase being more abundant than urease and phosphatase in the order listed. The addition of glyphosate and paraquat activated invertase and urease activities in several soils. Increments of invertase activity ranged from a very low increase (+4%) up to +204% in soils 11 and 14, respectively. Smaller increases were measured for urease. A general inhibitory effect (from 5% to 98%) was observed for phosphatase in the presence of glyphosate. The effects of atrazine and carbaryl on the three soil enzymes were evaluated against that exhibited by methanol, the solvent used for their solubilization. In almost all soils, atrazine further inhibited invertase activity with respect to the inhibitory effect shown by methanol. By contrast, consistent activation effects (from 61% to 10217%) were measured for urease with methanol alone and/or methanol-pesticide mixtures. Contradictory results were observed with phosphatase. Similarities found between the results obtained with enzymes in soils and those measured with synthetic enzyme complexes (e.g. free enzymes and/or clay-, organo-, and organo-clay-enzyme complexes) exposed to the same pesticides allowed some relationships between responses of soil enzymes to pesticides and soil properties to be hypothesized. | Kerry ME, Gregory AC, Bolwell GP (2001)
Differential behaviour of four plant polysaccharide synthases in the presence of organic solvents.
Phytochemistry 57, 1055-1060 [PubMed:11430978]
[show Abstract]
The behaviour of four membrane-bound glycosyl transferases involved in cell wall polysaccharide synthesis has been studied in relation to the effects of a graded series of organic solvents on their activity and type of product formed. Relative enzyme inhibition observed for some solvents was in direct relationship to the hydrophilicity of the product. This was in the order of arabinan synthase > callose synthase> xylan synthase > beta-1,4-glucan synthase. The former two were always inhibited, the xylan synthase rather less so. However, the beta-1,4-glucan synthase showed significant increases in substrate incorporation in the presence of solvents. A graded series of primary alcohols were much more effective in enhancing activity than acetone, ethyl acetate and dimethyl formamide. In the presence of the most effective solvent, methanol, there was considerable activation of beta-1,4-glucan production. This reciprocal nature of the behaviour of the beta-1,4- and beta-1,3-glucan synthases in organic solvent is supportive of recent molecular data that the two types of glucans are catalysed by separate enzyme systems. However, the results reported here do not totally negate the proposition that either enzyme is capable of synthesising the other linkage in minor amounts in vitro. | Nagasaki T, Yasuda S, Imai T (2001)
Preparation of antibody against agatharesinol, a norlignan, using a hapten-carrier conjugate.
Phytochemistry 58, 833-840 [PubMed:11684179]
[show Abstract]
In order to immunolabel heartwood extractives in Japanese cedar (Sugi, Cryptomeria japonica), we attempted to prepare antibodies against agatharesinol, a major norlignan of these heartwood extractives. Agatharesinol by itself is not antigenic due to its low-M(r), and thus was covalently bound to bovine serum albumin in order to synthesize an antigenic hapten-carrier conjugate (artificial antigen). The number of agatharesinol molecules per artificial antigen molecule was estimated as 27-28 by quantifying Lys in an acid hydrolysate of the artificial antigen by HPLC. Reaction between the artificial antigen and serum obtained from a rabbit immunized with the artificial antigen was competitively inhibited by agatharesinol, indicating the successful production of anti-agatharesinol antibodies. Inhibition by sequirin C, another major norlignan in Sugi, was weaker than that by agatharesinol. Furthermore, an EtOAc soluble fraction, which contains mainly norlignans, inhibited the reaction more strongly than any of the other fractions of Sugi heartwood extractives. Thus, the antiserum we have produced reacts most strongly with agatharesinol and recognizes norlignans almost selectively among Sugi heartwood extractives. | Huang YS, Held GA, Andrews JE, Rogers JM (2001)
(14)C methanol incorporation into DNA and proteins of organogenesis stage mouse embryos in vitro.
Reproductive toxicology (Elmsford, N.Y.) 15, 429-435 [PubMed:11489599]
[show Abstract]
Methanol (MeOH), a widely used industrial solvent and alternative motor fuel, has been shown to be mutagenic and teratogenic. We have demonstrated that methanol is teratogenic in mice in vivo and causes dysmorphogenesis in cultured organogenesis stage mouse embryos. Although MeOH is a product of endogenous metabolism in the gut and can be found in humans following consumption of various foods, elevated levels of methanol could lead to methylation of cellular macromolecules. DNA methylation has been demonstrated to suppress transcription of fetal genes and may also play an important role in genetic imprinting. Embryonal proteins are also potential targets for methanol-induced methylation. We investigated the potential of administered methanol to incorporate into and/or alter the methylation of embryonal DNA or to affect specific protein methylation. Gestational day 8 CD-1 mouse embryos were grown for 24 h in culture medium (CM) with 0, 4, or 8 mg MeOH + 20 microCi (14)C-MeOH/mL. At the end of the culture period, yolk sacs and embryos were separated for each treatment group. The DNA was purified by cesium chloride gradient centrifugation in the presence of ethidium bromide and (14)C incorporation was determined. Methylation of a selected gene, Hoxc-8, was assessed by using methylation-specific restriction enzymes. The (14)C activity was found superimposed over the DNA-containing fraction, indicating incorporation. DNA from embryos treated with 4 mg MeOH/mL CM gave the highest incorporation of (14)C-MeOH (8 mg/mL was growth inhibiting). Methylation of Hoxc-8 appeared to be increased in embryos treated with 4 mg MeOH/mL CM, but not in embryos treated with 8 mg MeOH/mL. Lack of incorporation of methylation at the higher concentration may be due to the failure of embryos to grow at this concentration of MeOH. The incorporation of (14)C-MeOH into embryo proteins was investigated by polyacrylamide gel electrophoresis (PAGE) and autoradiography. Incorporation of (14)C-MeOH into specific proteins was observed but the labeling specificity was not methanol dose-related. These results indicate that methyl groups from (14)C-MeOH are incorporated into mouse embryo DNA and protein. Our results further suggest that methanol exposure may increase genomic methylation under certain conditions which could lead to altered gene expression. | Lorberau CD, Pride JL (2000)
A laboratory comparison of two media for use in the assessment of dermal exposure to pesticides.
Applied occupational and environmental hygiene 15, 946-950 [PubMed:11141607]
[show Abstract]
In a laboratory study, gauze pads and Empore filters were compared for their ability to assess the dermal exposure of two insecticides (chlorpyrifos and diazinon) and five herbicides (atrazine, alachlor, metolachlor, cyanazine, and 2,4-D ethylhexyl ester). The analytes, when analyzed by gas chromatography with flame ionization detection, were found to have a linear dynamic range to at least 250 micrograms/mL. While a number of different solvents were examined for the desorption of the analytes, methanol was found to be the best solvent for the recovery of all the analytes from 16-ply gauze pads, while 20 percent ethyl acetate in hexane was the preferred solvent for the styrene divinylbenzene-impregnated Empore filters. Limits of detection (LODs) for the analytes were comparable for both media. For Empore filters, the LODs were 50 micrograms/sample for atrazine, alachlor, chlorpyrifos, diazinon, and 2,4-D ethylhexy ester, with 30 micrograms/sample for metolachlor, and 80 micrograms/sample for cyanazine. For gauze pads, the LODs were 40 micrograms/sample for metolachlor, 50 micrograms/sample for alachlor, diazinon, and 2,4-D ethylhexy ester, 60 micrograms/sample for atrazine and chlorpyrifos, and 80 micrograms/sample for cyanazine. Both gauze pads and Empore filters gave quantitative recovery for all analytes except chlorpyrifos and 2,4-D ethylhexyl ester under ambient conditions (18 degrees C, 70% relative humidity) for up to 30 days; these analytes required refrigeration for that period to reach over 90 percent recovery. To assess the effect of environmental conditions on the recovery of the analytes, samples of each media were spiked at about 125 micrograms per analyte/sample (except cyanazine which was spiked at 190 micrograms) and challenged for 8 hr under high (80%) and low (20%) humidity and high (40 degrees C) and low (5 degrees C) temperature conditions in an environmental chamber. While the Empore samples gave quantitative recovery after being challenged, recovery from the gauze pads was affected by environmental conditions, especially high temperature. Recovery from gauze pads was below 30 percent for some analytes under high temperature/high humidity conditions. | Reed TB, Lerner RM (1973)
Methanol: A Versatile Fuel for Immediate Use: Methanol can be made from gas, coal, or wood. It is stored and used in existing equipment.
Science (New York, N.Y.) 182, 1299-1304 [PubMed:17733096]
[show Abstract]
We believe that methanol is the most versatile synthetic fuel available and its use could stretch or eventually substitute for, the disappearing reserves of low-cost petroleum resources. Methanol could be used now as a means for marketing economically the natural gas that is otherwise going to waste in remote locations. If methanol were used as an additive to gasoline at a rate of 5 to 15 percent, for use in internal combustion engines, there would be an immediate reduction in atmospheric pollution, there would be less need for lead in fuel, and automobile performance would be improved. With increasing production of fuel-grade methanol from coal and other sources, we foresee the increasing use of methanol for electrical power plants, for heating, and for other fuel applications. We hope that a practical methanol fuel cell will be commercially available by the time that methanol becomes plentiful for fuel purposes. Methanol offers a particularly attractive form of solar-energy conservation, since agricultural and forest waste products can be used as the starting material. Indeed, at 1 percent conversion efficiency the forest lands could supply the entire present energy requirements of the United States. | ANASTASI A, ERSPAMER V (1962)
Occurrence and some properties of eledoisin in extracts of posterior salivary glands of Eledone.
British journal of pharmacology and chemotherapy 19, 326-336 [PubMed:14012711]
[show Abstract]
The posterior salivary glands of Eledone, alone among the tissues of this molluscan species, contain eledoisin, an endecapeptide with activity on blood vessels and extravascular smooth muscles. The salivary glands of Octopus vulgaris and O. macropus lack the polypeptide. Eledoisin is present, in amounts ranging from 20 to 160 mug/g fresh tissue, at all stages of growth and in every season; however, conspicuous differences in the eledoisin content were observed in different groups of animals. Eledoisin is fairly stable in intact salivary glands stored on ice. The most suitable solvent for its extraction is 70 to 80% methanol. Better results are also obtained with boiling diluted acetic acid, than with ethanol, whereas extraction with acetone gives unsatisfactory yields. Eledoisin is stable in neutral or slightly acid medium, but is rapidly destroyed by strong acids and even more rapidly by strong alkalis. It is quickly and completely inactivated by chymotrypsin, and somewhat more slowly and incompletely by trypsin. Carboxypeptidase is ineffective. Passage of crude salivary extracts of Eledone through an alumina column yields preparations of eledoisin which may be considered pure from a biological point of view. | (1923)
Methanol, the new name for Wood Alcohol.
Canadian Medical Association journal 13, 359 [PubMed:20314698] |
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